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DOI: 10.1055/s-2008-1042806
Facile Aromatic Claisen Rearrangement Catalysed by Tin(IV) Chloride
Publikationsverlauf
Publikationsdatum:
26. Februar 2008 (online)
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Abstract
Allyl aryl ethers undergo facile Claisen rearrangement under mild conditions catalysed by tin(IV) chloride.
Key words
Claisen rearrangement - allyl aryl ethers - Lewis acid - tin(IV) chloride
- 1
Claisen L. Chem. Ber. 1912, 45: 3157 - For reviews, see:
-
2a
Lutz RP. Chem. Rev. 1984, 84: 205 -
2b
Castro AMM. Chem. Rev. 2004, 104: 2939 -
3a
Brtyusova LYa.Ioffe ML. J. Gen. Chem.(U.S.S.R.) 1941, 11: 722 ; Chem. Abstr. 1942, 36, 430 -
3b
Cairns N.Harwood LM.Astles DP. J. Chem. Soc., Chem. Commun. 1986, 750 -
4a
Svanholm U.Parker VD. J. Chem. Soc., Chem. Commun. 1972, 645 -
4b
Harwood LM. J. Chem. Soc., Chem. Commun. 1983, 530 -
4c
Harwood LM. J. Chem. Soc., Perkin Trans. 2 1984, 2577 -
5a
Borgulya J.Madeja R.Fahrni P.Hansen H.-J.Schmid H.Barner R. Helv. Chim. Acta 1973, 56: 14 -
5b
Cairns N.Harwood LM.Astles DP.Alex O. J. Chem. Soc., Chem. Commun. 1986, 182 -
5c
Ito F.Fusegi K.Kumamoto T.Ishikawa T. Synthesis 2007, 1785 - 6
Kim KM.Kim HR.Chung KH.Song JH.Ryu EK. Synth. Commun. 1994, 24: 1859 -
7a
Sonnenberg FM. J. Org. Chem. 1970, 35: 3166 -
7b
Wipf P.Ribe S. Org. Lett. 2001, 3: 1503 - 8
Hayashi T.Goto M. Nippon Kagaku Kaishi 1978, 1007 ; Chem. Abstr. 1978, 89: 128852 - 9
Narasaka K.Bald E.Mukaiyama T. Chem. Lett. 1975, 1041 - 10
Sharma GVM.Ilangovan A.Sreenivas P.Mahalingam AK. Synlett 2000, 615 - 11 The only previous example of a tin(IV) chloride catalysed rearrangement of a deuterium-labelled allyl tolyl ether involved heating in decalin, see:
Feoktistov VM.Bunina-Krivorukova LI. Zh. Org. Khim. 1978, 14: 807 - 12
Wipf P.Rodriguez S. Adv. Synth. Catal. 2002, 344: 434 - 13
Pincock LA.Pincock AJ.Stefanova R. J. Am. Chem. Soc. 2002, 124: 9768 - 14
Krohn K.Bernhard S. Synthesis 1996, 699 - 15
Lecornué F.Olliver J. Synth. Lett. 2004, 1613 - 16
Benbow WJ.Rouse K.-R. J. Org. Chem. 2001, 66: 4965 - 17
Tsang YK.Brimble AM.Bremner BJ. Org. Lett. 2003, 5: 4425 - 18
Ollevier T.Mwene-Mbeja MT. Tetrahedron Lett. 2006, 47: 4051 - 19
Quefflec C.Bailly F.Cotelle P. Synthesis 2006, 768
References and Notes
7-Methoxy-2,5-dimethyl-dihydrobenzofuran (Entry 10)Obtained as a colourless solid. Crystallised from Et2O-PE, mp43-44 °C. 1H NMR (300 MHz, CDCl3): δ = 1.51 (d, J = 11.5 Hz, 3 H), 2.28 (s, 3 H), 3.02 (dd, A of ABX, J AB = 13.8 Hz, 1 H), 3.04 (dd, B of ABX, J BA = 13.8 Hz, 1 H), 3.87 (s, 3 H), 4.40 (sext, X of ABX, J AX = J BX = 6.6 Hz,1 H), 6.58 (s, 1 H), 6.60 (s, 1 H). 13C NMR (75 MHz, CDCl3): δ = 21.2, 24.9, 41.2, 56.0, 57.7, 110.3, 123.6, 123.8, 128.8, 141.6, 146.2. HRMS (ES+ve): m/z calcd for C11H14O2 [M + Na]+: 201.0892; found: 201.0889.